A Fond Look Back At Harry Styles' Dating History (2024)

Of all the major music artists right now, Harry Styles’ dating history has to be the most tabloid-worthy. Everyone wants to know who the ‘Watermelon Sugar’ star is dating, has dated, and will be seeing in the future (often something we end up deep in conspiracy theory-territory about based on song lyrics).

Ever since Styles shot to fame during his One Direction years, fans and non-fans alike have asked – who is Harry Styles’ girlfriend? Who is he dating now? Have Harry Styles and [insert gorgeous celebrity here] broken up? The questions go on and on, but theDon’t Worry Darling star is actually pretty quiet publicly when it comes to his relationship history. It’s rare you’ll see the man step out with a girlfriend in a public fashion, and in fact most of the information we have about Harry Styles’ dating history comes from paparazzi pictures, “sources” in gossip magazines and (most bizarrely) song lyrics.

Lets take a fond look back at some of Harry Styles’ most notable past relationships and dating history.

Olivia Wilde: 2020 – 2022

Styles’ most recent relationship was withDon’t Worry Darling director Olivia Wilde, and it was a tumultuous one. While the couple chose to keep their love story very quiet, that hush-hush desire blew up when rumours swirled that Styles had originally been hooking up with co-star Florence Pugh, and then even more so when Wilde’s ex-husband Jason Sudeikis was reportedly furious about the pair.

Some of Styles’ fans sent plenty of hate Olivia Wilde’s way, which both Wilde and Harry Styles addressed publicly. Wilde toldRolling Stone she doesn’t think all his fans are bad. “What I don’t understand about the cruelty you’re referencing is that that kind of toxic negativity is the antithesis of Harry and everything he puts out there. I don’t personally believe the hateful energy defines his fan base at all. The majority of them are true champions of kindness.”

While things seemed solid for a while, drama quickly returned when a former nanny for Sudeikis and Wilde did a tell-all interview with plenty of tea spilled, from alleged cheating, to a famous salad dressing that will forever be etched into our brains. In the interview, the former nanny alleged that one of Sudeikis’ last straws was when Wilde made her “special” salad dressing to take to Harry Styles. “I don’t know what was in it. Out of everything, he was like, ‘she made her special salad dressing and took it to him’.”

In the end, it seems the pressure that mounted due to all the circulating rumours was too much for the couple, who broke up in November 2022.

Camille Rowe: 2017 – 2019

Prior to dating Olivia Wilde, Harry Styles was linked to Victoria’s Secret model and actress, 33-year-old Camille Rowe. Styles and Rowe first started dating in 2017, when eagle-eyed (eared?) fans swore they could hear her voice in the background of an Instagram Story video posted by Harry Styles. Then, the pair were seen at a Fleetwood Mac concert in New York, where another attendee told Us Weekly that “they looked really cozy. They seemed like they were having a good time and were enjoying each other’s company.”

After two years of dating however, the couple broke up – and it was rumoured that Harry Styles may have cheated on Camille Rowe in the end.

Collaborator Tom Hull toldRolling Stone in August 2019 that Harry Styles’ break up with Rowe had a significant impact on the singer, who wrote multiple songs about their relationship for the albumFine Line. “He had a whole emotional journey about her, this whole relationship,” Hull told the outlet. “But I kept saying, ‘The best way of dealing with it is to put it in these songs you’re writing.'”

Rumoured Harry Styles songs about Camille Rowe include ‘Falling’ and ‘To Be Lonely’, but it’s ‘Cherry’ that saw fans going wild, with its seemingly direct references to Rowe and heart-achingly sad lyrics, like “don’t you call him baby/We’re not talking lately/Don’t you call him what you used to call me” and “I just miss your accent and your friends/Did you know I still talk to them?/Does he take you walking round his parents’ gallery?”.

Georgia Fowler: 2015

Back in October 2015, the internet went wild when New Zealand model and Victoria’s Secret star Georgia Fowler posted a Snapchat of her and Harry Styles playing Scrabble, of all things.

Their relationship seemed to be brief, lasting a few months around the end of 2015, but Fowler and Styles spent time at Babington House Hotel in Somerset, England so they could enjoy their relationship away from the paparazzi. “Harry wanted to spend some quality time with Georgia away from prying eyes,” sources close to the star told Stuff back then. “They kept to themselves and mostly spent their time in their room and garden, ordering food to the room instead of eating in the restaurant”.

The reason Georgia Fowler is such a notable figure in Harry Styles’ dating history is, well, once again because of his music. When his namesake album was released in 2017, the song ‘Kiwi’ spawned hundreds of headlines after people connected the dots between the title, and Fowler.

See, ‘Kiwi’ is slang for someone who hails from New Zealand, and given the timing between his relationship with Georgia Fowler and the release of the track, it seems pretty coincidental. However, when asked about it onThe Morning Show in 2017, Fowler was quick to shut down any rumours the track was about her, using one very fair reason.

“I definitely don’t have a baby!” she told hosts Larry Emdur and Kylie Gillies, referring to the chorus, which repeats the line ‘I’m having your baby/It’s none of your business’. Fair point.

Kendall Jenner 2013 – 2016

Aside from Taylor Swift (more on her relationship with Harry Styles later), Kendall Jenner is probably the ‘As It Was’ singer’s most famous ex-girlfriend. Their relationship was never really confirmed, nor was it very public, but it captured everyone’s attention because firstly, they’re probably two of the most beautiful people in the world, and secondly, because we always want to know who the Kardashians are dating, don’t we?

Their love story began way back in 2013 – a then 18-year-old Kendall Jenner was spotted in then 19-year-old Styles’ car after the couple had dinner at Craig’s in West Hollywood. While Jenner said she was “still single” shortly after this sighting, a few weeks later they were seen together again at the British Fashion Awards.

Next was a ski trip in California several months later. Yes, it was with friends – but reports flew that Harry Styles and Kendall Jenner only had eyes for each other. Things really seemed to heat up over New Year’s in 2014, though. Styles and Jenner were snapped on a yacht vacation, with a source tellingPeople “There has been a lot of flirting, touching and snuggling going on. They have acted like a couple. They look very cozy and happy.” The biggest moment came from Jenner’s sister Khloe Kardashian, however, who toldEntertainment Tonight that while she had vibes that they were dating, she wasn’t sure if they’d had “that talk” yet.

Things seemed to cool in early 2016, though – but it seemed like Harry Styles and Kendall Jenner broke up amicably, because they continued to spend time together as friends, with Styles even attending Jenner’s 21st birthday. When his namesake album launched in 2017, he pretty much dedicated the whole thing to her, tellingRolling Stone “She’s a huge part of the album. Sometimes you want to tip the hat, and sometimes you just want to give them the whole cap … and hope they know it’s just for them.”

Some Jenner-inspired songs?

Now, it seems Kendall Jenner and Harry Styles are just great friends. The pair appeared on The Late Late Show with James Cordenin 2019 to play a game of truth or dare, and most recently were rumoured to be leaning on each other as they navigated their respective break ups in 2022 – Styles with Olivia Wilde, Jenner with Devin Booker.

“Harry and Kendall have always stayed in touch, but in light of their recent splits, they have more time for one another. And Harry has had Kendall’s ear over his break-up with Olivia,” a source told The Sun. “Kendall is one of the few people to understand the level of fame and scrutiny which Harry endures. She is also dealing with her own tough time.”

Taylor Swift: 2012

Is this the relationship that created a thousand songs? Okay, maybe not athousand, but Harry Styles and Taylor Swift’s relationship definitely gifted us some pretty incredible tracks. That being said, it sounds like it was a pretty tumultuous on/off dating scenario.

Taylor Swift and Harry Styles first met at the 2012 Kid’s Choice Awards, but were first linked romantically in December 2012, when they were snapped in New York’s Central Park. That night, Swift went to the after party forOne Direction’s concert. Later in the month, fans spotted them kissing in Times Square at New Year’s Eve celebrations.

Just one month later, it seems the romance went out with a bang after an argument during a holiday in the Virgin Islands saw Taylor Swift call time on both the vacation and their relationship.

For such a short-lived relationship, Harry Styles and Taylor Swift’s love story sure did create a lot of drama. Swift’s1989 album is filled with songs fans are sure are about Styles, and she infamously dedicated her MTV Award for Best Female Video for ‘I Knew You Were Trouble’ from the album Red to “the person who inspired this song.” It’s widely believed this was a dig at Styles.

Taylor Swift has actually talked, albeit vaguely, about some of her music that’s allegedly about her relationship with Harry Styles.In 2014 onThe Morning Show, she spoke directly about ‘Style’, naturally the track that’s almost certainly about Harry Styles. “The song is actually bout those relationships that are never really done,” she told the hosts. “You always kind of have that one person who you feel like might interrupt your wedding and be like, ‘Don’t do it, we’re not over yet.’ I think everybody has that one person who kind of floats in and out of their life and the narrative is never truly over.”

For the record, Harry Styles seems fine with all these incredible songs that might be about him. He toldRolling Stone “I’m lucky if everything [we went through] helped create those songs. That’s what hits your heart. That’s the stuff that’s hardest to say, and it’s the stuff I talk least about. That’s the part that’s about the two people.”

Over the years it seems the two talented artists have mended fences – at the 2023 Grammy Awards, Taylor Swift was spotted walking over to Harry Styles to say hello, and she was one of few celebrities who remained standing as he accepted his award for Album Of The Year.

Caroline Flack: 2011

One of Harry Styles’ earliest relationships, and still one of his most controversial, was with UK presenter Caroline Flack. The reason it was so controversial? Harry Styles was just 17 years old when he started dating Flack, who at the time was 31. In her autobiography, Storm In A C Cup, Flack said “I already knew that he had a crush on me, he’d made it pretty obvious. He’d said it in magazines and he’d said it to friends.”

Things were apparently great until the day Harry Styles was snapped exiting Caroline Flack’s home. “Once that was out, it was open season. After that anyone could say anything.” She said she started getting death treats from One Direction fans, and the pressure caused by the media and Styles’ fanbase led to their split.

Tragically, Caroline Flack died by suicide in February 2020. Harry Styles didn’t make a public statement about her passing at first, but wore a black armband to the BRIT Awards that year, and during his performance wore a badge that said ‘treat people with kindness’, a sentiment Caroline Flack had shared prior to her death.